When anthracene is added to the reaction of chlorobenzene with concentrated NaOH at 350 °C, an interesting Diels–Alder adduct of formula C20H14 results. The proton NMR spectrum of the product shows a singlet of area 2 around δ 3 and a broad singlet of area 12 around δ 7. Propose a structure for the product, and explain why one of the aromatic rings of anthracene reacted as a diene.
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